What stands out worked out from the figures below

Weston has the most expensive homes ($1694k median).

Windsor has the most affordable homes ($208k median).

What matters to you?

Pick a few. We’ll pull those rows to the top and mark which town comes out ahead on each. There’s no overall score: what matters is up to you.

Raising kidsAffordabilityOwning a homeShort commuteWorking from homeYounger crowdSettled, older crowdGrowing town

Measure	Weston	Windsor
People
Population	11,579Highest	3,554Lowest
Growth since 20102010 → 2020 census	+5.2%Highest U.S.: +7.4%	+0.2%Lowest U.S.: +7.4%
Median age	44.9±2.1Highest 15% above U.S.	44.8±6.5Lowest 15% above U.S.
	Weston and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	26%±3.8Highest U.S.: 22%	19.5%±5.2Lowest U.S.: 22%
	Weston and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	20%±2.8Lowest U.S.: 17.2%	29.7%±6.9Highest U.S.: 17.2%
	Windsor and Weston are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	84.3%Highest U.S.: 35.7%	39.7%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	9.8%±1.6Highest U.S.: 6.4%	0.7%±0.8Lowest U.S.: 6.4%
Cost of living
Household incomemedian	$250,001Highest 210% above U.S.	$52,484±$11kLowest 35% below U.S.
Home valuemedian, owner-occupied	$1,694,400±$263kHighest 409% above U.S.	$207,500±$31kLowest 38% below U.S.
Rentmedian gross, monthly	$2,085±$809Highest 48% above U.S.	$1,026±$89Lowest 27% below U.S.
Property taxmedian, yearly	$10,000+Highest at least 221% above U.S.	$5,209Lowest 67% above U.S.
Renters paying 30%+of income on rent	69%±23Highest U.S.: 51.1%	31.5%±17Lowest U.S.: 51.1%
	Weston and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	2.9%Lowest U.S.: 12.5%	7.8%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	87.5%Highest U.S.: 65.2%	57.8%Lowest U.S.: 65.2%
Typical home builtmedian year	1964Highest 16 yrs older than U.S.	1945Lowest 35 yrs older than U.S.
Getting to work
Average commuteone way	27 minHighest about the U.S. average	23 minLowest 14% below U.S.
Work from home	29.1%±5.2Highest U.S.: 15.1%	10.3%±5Lowest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#9 of 282 in MA	#61 of 70 in VT
School district	Weston	—
High school in town	Weston High	—
Students per teacherat that high school	10.9	—
On TownTapestry
Old photos in History	None yet	12 photos →

U.S. average · Sources: U.S. Census Bureau, American Community Survey 5-year estimates 2020–2024; 2010 & 2020 decennial census; NCES Common Core of Data. “±” is the Census margin of error. Property tax is top-coded by the Census at $10,000+. School rank compares math and reading proficiency against the state average.